Chloroacetyl chloride → HCID 67078123, compound
Reaction equation
[NH2:1][C@@H:2]([CH2:5][O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:3][OH:4].C(N(CC)CC)C.[Cl:21][CH2:22][C:23](Cl)=[O:24]>C(#N)C.CO>[CH2:7]([O:6][CH2:5][C@H:2]([NH:1][C:23](=[O:24])[CH2:22][Cl:21])[CH2:3][OH:4])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1Participants
6
Reactant 3
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- -10 °C
Procedure
(2R)-2-Amino-3-(benzyloxy)propan-1-ol (2.18 g) was dissolved in acetonitrile (38 ml) and methanol (7 ml), and triethylamine (2.0 ml) was added. The atmosphere was replaced with nitrogen, and then the mixture was cooled to −10° C. A solution of chloroacetyl chloride (1.05 ml) in acetonitrile (9 ml) was added dropwise thereto, and the mixture was stirred for 20 hours to be gradually warmed to room temperature. The reaction solvent was distilled off, and the residue was directly purified by silica gel column chromatography (developed with ethyl acetate-hexane) to give the title compound (2.26 g).
Workup
- temperatureto be gradually warmed to room temperature
- distillationThe reaction solvent was distilled off
- customthe residue was directly purified by silica gel column chromatography (developed with ethyl acetate-hexane)
Sources & evidence
- ORD record
- ord-82063818d3194f4b8a6247a5dd49b930
- Source dataset
- uspto-grants-2014_07
- Patent number
- US08785438B2
Reaction notes
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